Siesta Key, FL Homes

/33
$474,500
- 1 Bed
- 2 Baths
- 780 Sq Ft
1250 N Portofino Dr Unit 304, Sarasota, FL 34242

Wake up to sunrises over the marina, spend your afternoons boating or relaxing on the powdery sands of Siesta Key Beach, and unwind in the evening on your enclosed balcony, enjoying the tranquil views of the boats below and colorful evening skies. Located in Siesta Harbor, this furnished 1-bedroom, 2-bath condo offers a comfortable, coastal lifestyle just steps from the water. Beautifully updated

Marci McFarland MICHAEL SAUNDERS & COMPANY

1250 N Portofino Dr Unit 304, Sarasota, FL 34242
/38
$5,000 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242

Enjoy your vacation on Siesta Key in this spacious three bedroom/two bathroom vacation rental. This condo is turnkey furnished including washer/ dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.

Andy Moore GULF COAST REALTY & MANAGEMENT

1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242
/27
$1,200,000 Sold Mar 12, 2025
- 2,181 Sq Ft
- $550/SF
- 30 Days On Market
- 3 Beds
- 2 Baths
- Built 1972
579 Commonwealth Ln, Sarasota, FL 34242

LARGE LOT ON SIESTAS GRAND CANAL! with seawall, boat dock and lift. Sited on a quiet cul-de-sac with mature trees and newer/ larger homes. Just a short ride to Siesta beach and village. New dock built 2010 and lift new in 2022. This property did survive flooding during recent storms, it is sold at land value so the home is a gift. No warranties, representations or disclosures available as buyer

Bob Stahlschmidt II BRIGHT REALTY

579 Commonwealth Ln, Sarasota, FL 34242

/49
Est $709,802 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 975 Sq Ft
1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

/70
$7,495,000
- 7 Beds
- 7.5 Baths
- 3,388 Sq Ft
89 Avenida Messina, Sarasota, FL 34242

Welcome to Seashell Esta, a stunning coastal retreat nestled in the heart of Siesta Key, offering the epitome of luxury living. Boasting 7 bedrooms and 7.5 baths, this brand-new home is turnkey furnished is only steps to the beach and offers an elevator. Step inside and discover a haven of sophistication, where chic, modern furnishings grace every corner. The private balconies and rooftop deck

Jay Travis RE/MAX ALLIANCE GROUP

89 Avenida Messina, Sarasota, FL 34242
/29
$5,700 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242

Charming 2 bedroom/ 2 bath Condo just a short walk to the beach. Come enjoy our key-west style condo with a very rare 2 car garage. Two swimming pools, tennis court, pickleball, workout room and fishing dock round out the amenities on our lushly landscaped property. Nestled between palm trees, this ground floor condo does not have a unit above it. Impeccably clean and comfortable with a fully

Andy Moore GULF COAST REALTY & MANAGEMENT

1219 Siesta Bayside Dr Unit 1219C, Sarasota, FL 34242
/28
$780,000 Sold Mar 11, 2025
- 1,492 Sq Ft
- $523/SF
- 99 Days On Market
- 3 Beds
- 2 Baths
- Built 1969
5133 Sandy Beach Ave, Sarasota, FL 34242

*FEMA APPRAISAL STRUCTURE VALUE IS $446,000* Presenting a unique restoration or new build opportunity in the heart of coveted Siesta Key. This home sits on an expansive 10,000+ square foot lot just moments from Siesta Key's world-renowned white quartz sand beaches. While the property has sustained some damage from recent storms, it offers solid bones and incredible potential for those looking to

Joanna Benante MICHAEL SAUNDERS & COMPANY

5133 Sandy Beach Ave, Sarasota, FL 34242

/41
Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,463 Sq Ft
5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

/66
$1,200,000
- 5 Beds
- 3 Baths
- 2,511 Sq Ft
105 Island Cir, Sarasota, FL 34242

This land is a RARE BEAUTY, are you dreaming of building your home where you and your family enjoy a lifestyle uniquely created for yourselves? IMAGINE a majestic home with a standalone guest house, alluring pool and gardens privately nestled among the palm trees. This property offers 2 lots, 0.45 acres / 19,456 sf. Palm Island is a community with only 298 homes where the residents enjoy

Linda Scheller COLDWELL BANKER REALTY

105 Island Cir, Sarasota, FL 34242
/34
$8,100 per month
- 2 Beds
- 2 Baths
- 1,420 Sq Ft
- Condo for Rent
1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242

Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedrooms and two bathrooms, this meticulously designed residence seamlessly blends coastal elegance with modern comfort.Step into a sunlit living space adorned with coastal-inspired décor,

Andy Moore GULF COAST REALTY & MANAGEMENT

1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242
/2
$390,000 Sold Mar 06, 2025
- 522 Sq Ft
- $747/SF
- 159 Days On Market
- 1 Bed
- 1 Bath
- Built 1978
5955 Midnight Pass Rd Unit 12E, Sarasota, FL 34242

SUPERB DAILY VACATION RENTAL on the world-famous SIESTA KEY known for sugar sand beaches, fine dining, excellent shopping, tons of nightlife and entertainment in Siesta Key Village. Cobalt blue waters are just across the street with a gated and deeded access to the sand where you can spend your day swimming, sunning and building castles on this perfect island on the gorgeous Gulf of Mexico. SEA

Michelle Hennessy PREFERRED SHORE LLC

5955 Midnight Pass Rd Unit 12E, Sarasota, FL 34242

/38
Est $640,286 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,271 Sq Ft
199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

/65
$1,200,000
- Land
- 0.45 Acre
- $2,666,667 per Acre
105 Island Cir, Sarasota, FL 34242

This land is a RARE BEAUTY, are you dreaming of building your home where you and your family enjoy a lifestyle uniquely created for yourselves? IMAGINE a majestic home with a standalone guest house, alluring pool and gardens privately nestled among the palm trees. This property offers 2 lots, 0.45 acres / 19,456 sf. Palm Island is a community with only 298 homes where the residents enjoy

Linda Scheller COLDWELL BANKER REALTY

105 Island Cir, Sarasota, FL 34242
/24
$7,600 per month
- 2 Beds
- 1 Bath
- 959 Sq Ft
- Condo for Rent
1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242

Gulf and Bay Club Bayside is one of the most attractive condominium units on Siesta Key. This beautifully remodeled unit offers luxury accommodations at a reasonable cost. Offering a beautiful lake view and steps to the resort-style pool. You will enjoy your stay every minute.Enjoy all of the luxurious amenities this unit has to offer, from comfortable King size bed to the comfy

Andy Moore GULF COAST REALTY & MANAGEMENT

1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
/2
$600,000 Sold Mar 03, 2025
- 816 Sq Ft
- $735/SF
- 31 Days On Market
- 1 Bed
- 1 Bath
- Built 1970
797 Beach Rd Unit 305, Sarasota, FL 34242

Here's your chance to own your little slice of paradise directly across from the most beautiful beach in the country! This updated, turnkey furnished condo has great rentals, as well as a fabulous location on Siesta Key. Close to the village of Siesta, with its shops and restaurants, directly across from world famous Siesta Key Beach, this complex offers a pool, club house, fitness room, gated

Karen Chandler MICHAEL SAUNDERS & COMPANY

797 Beach Rd Unit 305, Sarasota, FL 34242

/31
Est $576,285 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 900 Sq Ft
1110 S Moonmist Ct Unit M-11, Sarasota, FL 34242

1110 S Moonmist Ct Unit M-11, Sarasota, FL 34242

/62
$1,450,000
- 2 Beds
- 2 Baths
- 1,334 Sq Ft
5920 Midnight Pass Rd Unit 406, Sarasota, FL 34242

Sarasota Surf and Racquet Club – Tower Building - Exceptional Beachfront Living on Siesta KeyDon’t miss this rare opportunity to own a beautifully appointed 2-bedroom, 2-bathroom condo in the highly sought-after Tower Building of Sarasota Surf and Racquet Club, located directly on Crescent Beach, Siesta Key’s world-famous stretch of powdery white sand.Situated on the 4th floor, this

Greg Hudson COLDWELL BANKER REALTY

5920 Midnight Pass Rd Unit 406, Sarasota, FL 34242
/18
$7,700 per month
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
- Condo for Rent
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242

Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops

Andy Moore GULF COAST REALTY & MANAGEMENT

1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
/2
$623,000 Sold Feb 28, 2025
- 1,352 Sq Ft
- $461/SF
- 37 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
1137 Lake House Cir Unit C215, Sarasota, FL 34242

Reduced! The Best Price for a 2 Bed with a Garage on the Key! Your place at the beach needs to be Our House at The Beach. This 2 bed 2 bath 2nd floor unit with it's own 1 car garage is beautifully updated with carefree bamboo floors in all the living space and ceramic tile in the baths, oversize crown moldings and base trim. It offers lake views with a fountain and a twenty-foot-wide balcony

Mike Winger RE/MAX PLATINUM

1137 Lake House Cir Unit C215, Sarasota, FL 34242

/69
Est $691,960 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
5855 Midnight Pass Rd Unit 704, Sarasota, FL 34242

5855 Midnight Pass Rd Unit 704, Sarasota, FL 34242

/63
$6,400,000
- 4 Beds
- 4.5 Baths
- 4,946 Sq Ft
156 Givens St, Sarasota, FL 34242

Siesta Key modern gem directly on Big Pass with panoramic sunset views of the Gulf of America. New Roof, New Air Conditioning Units, New Water Heaters, New Pool Equipment, New Wood Flooring and Landscaping. Enjoy the expert design work of renowned Architect, Guy Peterson, executed with master craftsmanship in this 4 bedroom, 4.5 bath home in a private, gated enclave of two modern masterpieces

Ash Keiver 19TH HOLE PROPERTIES

156 Givens St, Sarasota, FL 34242
/89
$4,700 per month
- 3 Beds
- 3 Baths
- 1,867 Sq Ft
- Condo for Rent
4900 Ocean Blvd Unit 501, Sarasota, FL 34242

Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the

Beth Dilley ASCENDIA REAL ESTATE

4900 Ocean Blvd Unit 501, Sarasota, FL 34242
/2
$8,100,000 Sold Feb 27, 2025
- 5,282 Sq Ft
- $1534/SF
- 145 Days On Market
- 4 Beds
- 7 Baths
- Built 2024
3960 Roberts Point Rd, Sarasota, FL 34242

Nestled within the coveted north end of Siesta Key, this extraordinary residence boasts a blend of modern & contemporary elegance. Situated on an expansive lot spanning approximately 0.45 acres along the scenic Roberts Point Rd, the home welcomes you through private gates into your own secluded sanctuary. Possessing a spacious driveway with garages accommodating up to 7 vehicles (5-car garage

Tammy Dentici BRIGHT REALTY

3960 Roberts Point Rd, Sarasota, FL 34242

/6
Not Listed For Sale
0 Venice Ln Unit 4,5, Sarasota, FL 34242

0 Venice Ln Unit 4,5, Sarasota, FL 34242

/22
$899,000
- Land
- 0.27 Acre
- $3,329,630 per Acre
717 Treasure Boat Way, Sarasota, FL 34242

Looking for the perfect slice of Siesta Key paradise to make your own? This property offers 110’ of street frontage and is situated on just over ¼ acre lot with majestic trees offering shade, privacy and tons of character. For families, the highly rated Out-Of-Door Academy is just a few blocks away for Pre-K through Grade 5. The #1 Siesta Key Beach is located approximately 1 mile from the front

Ian Addy, PA MICHAEL SAUNDERS & COMPANY

717 Treasure Boat Way, Sarasota, FL 34242
/35
$8,200 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

Andy Moore GULF COAST REALTY & MANAGEMENT

1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
/2
$850,000 Sold Feb 26, 2025
- 2,832 Sq Ft
- $300/SF
- 34 Days On Market
- 3 Beds
- 2 Baths
- Built 1952
4431 Ocean Blvd, Sarasota, FL 34242

Beautiful home located in the heart of picturesque Siesta Key. This home offers the perfect blend of island living and untapped potential. While recently impacted by Hurricanes Helene and Milton, this property remains a rare gem with endless possibilities to restore and reimagine your dream coastal retreat. Located just minutes from world-famous Siesta Key Beach, this property is your chance to

Shawn Judy FLORIDA SUN & SAND REALTY

4431 Ocean Blvd, Sarasota, FL 34242

/20
Est $589,784 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 860 Sq Ft
1600 Cove II Place Unit 423, Sarasota, FL 34242

1600 Cove II Place Unit 423, Sarasota, FL 34242

/42
$899,000
- 2 Beds
- 2 Baths
- 1,978 Sq Ft
717 Treasure Boat Way, Sarasota, FL 34242

Looking for the perfect slice of Siesta Key paradise to make your own? This 2 bed/2 bath home is situated on just over ¼ acre lot with majestic trees offering shade, privacy and tons of character. The newly carpeted living room opens up to the Florida Room for the perfect marriage of indoor/outdoor living. An oversized screened patio just off the kitchen provides the perfect opportunity for

Ian Addy, PA MICHAEL SAUNDERS & COMPANY

717 Treasure Boat Way, Sarasota, FL 34242
/27
$6,300 per month
- 2 Beds
- 2 Baths
- 959 Sq Ft
- Condo for Rent
1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242

Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,

Andy Moore GULF COAST REALTY & MANAGEMENT

1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
/2
$540,000 Sold Feb 26, 2025
- 1,165 Sq Ft
- $464/SF
- 30 Days On Market
- 2 Beds
- 2 Baths
- Built 1976
5855 Midnight Pass Rd Unit 511, Sarasota, FL 34242

Welcome to Harbor Towers Yacht & Racket Club on Siesta Key! This 2-bedroom, 2-bathroom condo offers an exciting opportunity to create your dream coastal retreat. While the interior needs updating, the potential is endless. The open floor plan offers a spacious living area, two generous bedrooms, and a Florida room perfect for taking in the serene surroundings. Sold fully furnished, this condo is

Molly Higdon KELLER WILLIAMS ON THE WATER S

5855 Midnight Pass Rd Unit 511, Sarasota, FL 34242

/23
Est $688,188 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
137 Avenida Messina Unit 1, Sarasota, FL 34242

137 Avenida Messina Unit 1, Sarasota, FL 34242

/37
$1,250,000
- 3 Beds
- 4 Baths
- 3,050 Sq Ft
5324 Siesta Ct, Sarasota, FL 34242

Welcome to this striking contemporary residence tucked away in the highly sought-after community of Siesta Cove—an established subdivision on Siesta Key. Located just moments from the powdery sands of Siesta Key Beach and Siesta Key Village. Built in 1980 and thoughtfully updated, this three-bedroom, four-bathroom home sits on a beautifully designed eco-friendly yard with tropical and native

James Gammello WILLIAM RAVEIS REAL ESTATE

5324 Siesta Ct, Sarasota, FL 34242
/54
$9,500 per month
- 3 Beds
- 2 Baths
- 1,835 Sq Ft
- Condo for Rent
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

Andy Moore GULF COAST REALTY & MANAGEMENT

1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
/2
$925,000 Sold Feb 25, 2025
- 2,346 Sq Ft
- $394/SF
- 21 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1962
431 Island Cir, Sarasota, FL 34242

Exceptional investment opportunity with tons of equity in the exclusive Palm Island neighborhood of Siesta Key. While partially affected by the recent hurricane, over $50,000 has been invested in professional repairs, including removal of 4 feet of drywall where needed. AC 2018. Metal roof.The property is well-maintained with ongoing pool service, yard care, and general upkeep.

Steven Koleno BEYCOME OF FLORIDA LLC

431 Island Cir, Sarasota, FL 34242

/25
Not Listed For Sale
0 Commonwealth Dr Unit A4538307, Sarasota, FL 34242

0 Commonwealth Dr Unit A4538307, Sarasota, FL 34242

/47
$699,900
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242

Coastal living at it's best at Harbor Towers Yacht & Racquet Club. You will fall in love from the moment you enter this gated premier waterfront paradise on Siesta Key which recently completed a $13 million, four-year hurricane hardening and structural upgrade program in 2024, meeting all new safety standards for hurricane/wind protection. WOW this beautifully furnished 2-Bedroom, 2-Bathroom

Susan Retzke RE/MAX PLATINUM

5855 Midnight Pass Rd Unit 204, Sarasota, FL 34242
/35
$7,400 per month
- 2 Beds
- 2 Baths
- 1,280 Sq Ft
- Condo for Rent
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle

Andy Moore GULF COAST REALTY & MANAGEMENT

1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
/2
$1,150,000 Sold Feb 25, 2025
- 1,446 Sq Ft
- $795/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
5300 Ocean Blvd Unit 704, Sarasota, FL 34242

Welcome to your dream coastal retreat! This condo offers breathtaking views of the Gulf of Mexico, placing you just steps away from a deeded beach access and the sparkling shoreline. Located in the vibrant heart of Siesta Key Village, this property offers unparalleled access to the best dining, shopping and entertainment, all just a few steps away from your door. Whether you're savoring the

Samantha Jennen PREFERRED SHORE LLC

5300 Ocean Blvd Unit 704, Sarasota, FL 34242

/46
Est $671,355 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
5855 Midnight Pass Rd Unit 708, Sarasota, FL 34242

5855 Midnight Pass Rd Unit 708, Sarasota, FL 34242

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